Advice About Sending Email

I’ve been using email on the Internet (and its predecessor, the ARPAnet) for 32 year.  Here’s some advice from my experience.

The Prime Directive: Never send email when you’re angry.  Never, ever.  It always backfires and you always regret it. Trust me on this.

The rest of these recommendations apply primarily when you’re sending mail to anyone who isn’t a close friend.

Do not use sarcasm on mailing lists.  Remember your tone of voice is not available to indicate that what you’re saying is sarcasm.  Inevitably, a few people on the list will take what you say literally, and then you’ll have to underke the boring job of correcting everyone’s misimpression.

Be very polite.  You almost can’t be too polite.  Because your facial expressions and tone of voice are not present, it’s easy to write something that will seem demanding or commanding.

Know the difference between “Reply” and “Reply All”, and be careful to always use the appropriate one.

Be careful to address your mail to the right person!  The automatic name-completion feature in many of the good mail clients can sometimes complete to a name that’s not what you expected.

Some people have separate home and company email addresses.  Send personal mail to the home address.

Be careful about giving out someone else’s personal email address.  Some people do not like to have their email addresses be well-known.  So treat anyone else’s email address as if it were confidential information, until you get permission to distribute it.

When sending mail to many individuals, address the mail to yourself, and BCC it to everyone else.  This way, the recipients cannot see the email addresses of the other recipients, thus protecting their privacy.

Make your subject lines descriptive and clear.  If you’re replying, keep the same subject line (don’t worry about the “Re:”) so that mail readers can see which mail is grouped with which.  If you’re communicating with friends, clever subject lines can be quite an art form and source of innocent merriment.

Save away all of your interesting email.  It’s very handy to be able to refer to it when you subsequently communicate with the same person, or company.

Keep your email on your own computer.  Leaving it on a net server is too much of a risk to your privacy.  Even if you like Google (which I do) and trust them (which I pretty much do), you never know if conditions will change in the future, and by then it’s too late.

For very sensitive email, encryption is a good idea.  Sadly, there isn’t an easy-to-use standard.  I use the free version of AxCrypt from Axantum ; it’s only for Windows, unfortunately.  There are plenty of others.  Of course, the person to whom you are sending mail must also install the software, and you must have a shared passphrase.  As long as you’re going to the trouble to encrypt, use a long passphrase for better security.

Please feel free to use the Comments below to add other good advice.

15 Responses to “Advice About Sending Email”

  1. Vinay Says:

    Always use plain text.

  2. John Cowan Says:

    Use PGP-compatible encryption if you are going to encrypt, even if it’s painful to use. There is and always will be software available to decrypt it (provided you have not forgotten the passphrase), which is not necessarily true of other schemes.

    Save both incoming and outgoing email, though you need not save *all* incoming email, of course, particularly email sent to public mailing lists — they almost always have public archives.

    A: Because it puts the answer before the question.
    Q: Why is top-posting bad?

  3. David Says:

    For crypto, OpenPGP software is great, it is well integrated with quite a few MUAs, and does not require a shared secret like a passphrase. S/MIME also works pretty well for thse purposes, and it works even in Outlook Express ;-) though you need SSL certificates, but you could generate self-signed ones or use something like http://cacert.org

  4. Joshua Kugler Says:

    Regrading sending to every via BCC. The only problem with this is that some systems used to, and maybe still do, drop the e-mail silently if the user to whom you are sending is not in the To or CC field. I know AOL used to do this, they still might. Caveat sender.

  5. Vinay Says:

    Use Mutt. (http://www.mutt.org/)

  6. Steven G. Atkinson Says:

    While you said it, some people may need to be explained in detail, don’t use acronyms. It might be obvious to you, but those inn receipt might either use it as meaning something else or have no idea what it means.

    And for goodness sakes don’t use IM shorthand. A business email should be treated as a formal letter.

    Proofread before you hit the send button.

    Author of:
    http://SMBTechTips

  7. jaans Says:

    Thanks for the tips. I find the one near the end interesting, about saving all your mail on your own computer.

  8. Top Posts « WordPress.com Says:

    [...] Advice About Sending Email I’ve been using email on the Internet (and its predecessor, the ARPAnet) for 32 year.  Here’s some advice [...] [...]

  9. Stas Sushkov Says:

    There’s also an email checklist proposed by Seth Godin: http://sethgodin.typepad.com/seths_blog/2008/06/email-checklist.html

    It’s pretty much interesting reading both yours and Seth’s advices. Imho, they just accomplish each other.

    Thank you.

  10. Name required Says:

    Don’t. Send. HTML. Email.

    /bites table in frustration

  11. dan thomas Says:

    Thanks for the tips. about saving all your mail on your own computer.

  12. Savjeti za slanje email poruka « Ne tako otvoreni blog Says:

    [...] Septembar 1, 2008 at 10:59 am · Filed under Linkovi http://danweinreb.org/blog/advice-about-sending-email [...]

  13. Orgalasteetry Says:

    Thanks the author!

  14. Dan Weinreb Says:

    From an article in the Boston Globe by Alex Beam:

    http://www.boston.com/ae/media/articles/2009/06/19/paper_vs_computer_screen

    Even the best computer screens are harder on the eyes than the paper page is. Jakob Nielsen, a Web usability researcher, reports that we generally read 25 percent more slowly on the screen. I read more quickly on the screen and edit out about 40 percent of what appears before my eyes. If you haven’t told me what you want by line four of your e-mail, trust me, I didn’t get the message.

  15. Danny Bloom Says:

    Alex Beam deserves a Pulitzter for that column, especially this remark:

    “If you haven’t told me what you want by line four of your e-mail, trust me, I didn’t get the message.”

    So true!